I know, I know. Many of you don’t have day jobs to return to. Perhaps I should have called this section “When To Return to A Day Job,” because there are always day jobs lurking out there, especially bad day jobs, the kind that work you to death and don’t pay the rent, let alone benefits or vacation days.

I’ve been planning to do this section ever since I wrote the “When To Quit Your Day Job” section in May.Because most freelancers bounce back and forth between a day job and no day job for years.

Let’s talk about why.

First, freelance work is unreliable.I’ve discussed this in previous sections.(I could go into a long diatribe about day jobs being unreliable as well, but you all get that now; you’ve lived through the last year just like the rest of us.) Freelance work is unreliable in a variety of ways: You don’t get paid on time or you don’t get paid as much as you planned; you don’t get as much work as you hoped or the work takes longer than you expected; and you need to learn how to do the freelance work.

That sounds silly to those of you who haven’t been reading the guide.Right now, turn back to the sections on Time and Priorities to see exactly what I’m talking about.

In short, the minute you quit your day job, you think you’ll have more than enough time to get the work done. So you procrastinate. Without someone else to schedule your time, you allow entire days to go by without accomplishing anything.You have to learn how to manage yourself so that you can actually do your new job which is, after all, working for yourself.

But, as we’ve been discussing in the setbacks sections (here are the links for one, two, and three), bad things happen. Sometimes those bad things are so severe, you have to go back to work.

For someone else.

Going back to a day job is tough.

First, you have to figure out if you should go back.Have you had some of the setbacks described in the setback section? Are you out of money? Has a physical disaster struck? Are you utterly demoralized due to some horrible business trauma?

Then maybe it’s time to let someone else worry about keeping a business alive. You go and man a desk or tend bar or attach yourself to a university press as a copy editor. Report at nine, leave at five, and hope you get an hour for lunch.

Rest, recuperate. Save money.

Then plan your return to the freelancing business slowly and with forethought.

We’ll get to that part in a minute as well, but let’s concentrate on deciding to go back first. Because there are some major things you have to consider.

1. Are you running away? Has the going gotten so tough in your freelance business that you’re actually dreaming of working for a corporation again? Is this a temporary feeling or have you discovered that you’re not suited emotionally to being your own boss?

A lot of people aren’t able to freelance.I know half a dozen local professional writers who actively shudder at the thought of doing without a day job. These writers actually make more money at their writing, but they like the security and structure of the paycheck and they can’t abide the idea of getting paid “whenever.”Work outside the home gives them structure. A paycheck from an outside business, however small, gives them a base.

Yes, it limits how much work they can do on their freelance business, but it also saves them from the extreme lows that come with such work, those scary moments when you have no idea how to pay the rent or when the next check will actually show up.

But let’s assume you’re not one of those people.Let’s assume you love freelancing—or you did, until something bad happened. That something bad could be a horrible occurrence, like a theft, or it could be prolonged stress from a series of late payments.

Whatever that something is, it has made you want to give up freelancing and get a “real” job.

(An aside: I really hate the idea expressed by “a real job.” My job is real, and is damn hard. It’s not brain surgery [thank heavens—you don’t want a dyslexic woman with a short attention span operating on your brain] but it takes more time and effort than almost any other job I’ve ever held—including the fulltime reporting/radio work. My job is real; it’s just unconventional and hard to categorize. And that’s the difference between a “real” job and freelance work. A real job is easy to define. Freelance work isn’t.)

Before you quit freelancing, go through a thorough analysis. Will you be able to keep your current clients or meet your contracts while you have that day job? Can you shut down your freelance business with no harm to your reputation? Will you be able to collect on those back debts if you shut down? (Dean kept Pulphouse Publishing alive all by himself [from a staff of 19] in order to collect more than $100,000 of back debt so he could pay off the company’s creditors. If he hadn’t done that, the $100,000 would never have crossed our desk.)

Be brutal and honest with yourself. Ask yourself whether or not your desire to return to the day job is a legitimate response to your current crisis or if it’s just you looking for the easy way out.

I’ve done it both ways. I’ve taken day jobs as a legitimate response to financial crisis, and I’ve run to day jobs because I didn’t trust my freelancing ability.The ones I ran to because I didn’t trust my own ability didn’t last long, as I realized that I am both unsuited to corporate work and that, even in my twenties, I could earn more writing than I ever did at a salaried position.I just had to hustle more.

The jobs I went to as a response to a legitimate financial crisis lasted longer.I stayed until the crisis was well past.Each paycheck went to repaying debts or keeping a roof over my head. Those jobs I did gratefully (or as gratefully as I could, given who I am) and while I did them, I continued to freelance.

I stopped freelancing at the run-scared jobs, and then busted out of those quickly when I realized I was much happier working for myself.

I like to say I’m unemployable, but I still get job offers—two just last summer for editing positions.I’m old enough now that I recognize the looming disaster. I doubt I’d have the patience of my youth. I’d probably bust out of those new jobs in less than a week. Once the novelty wears off, I’d be gone.

But if you’ve never gone fulltime freelancing before, you have no idea what your response to that uncertain lifestyle will be. After you’ve tried it, you’ll have some idea. That’s where the honesty comes in.

My writer friends who need their day jobs get nervous whenever I talk about pushing back bills to cope with a $20,000 check that’s overdue. They understand that a day job isn’t secure, but they know that a day job often has the illusion of security, and for them, that’s enough.

Freelance work has no illusion of security. You deal with uncertainty every single day. What will I work on next? Where will I be tomorrow? Who’ll pay me next March?

In addition, there’s the personal insecurity. Sure, people are buying my work now but will they buy it two years from now? Will tastes change? Will a new contractor (a better contractor) come into the area and steal my clients? Will people continue to value my work?

Not too long ago (a few years, maybe more [I’m being vague to protect the guilty]), I had a series of setbacks. Bad ones. Two publishing deals went south. I hired the world’s most incompetent agent and didn’t discover how bad this person was for 18 months. I lost a lot of money when a publisher went bankrupt. And I started getting the nastiest letters I’d ever gotten from editors—even nastier than when I started as a know-nothing beginner.

Eventually, I learned that the nasty letters weren’t directed at me, but at the incompetent agent, who managed to screw up most everything (and anger people in the process).I managed to squeeze some money out of that bankrupt publisher, one of the few writers to do so. And slowly, I rebuilt from the publishing disasters that befell me at the same time.

I’d been through similar things before. I’d never had an agent who was that incompetent, but I’d had bad employees. I knew how to rebuild from that. It took a while to recover from the blows to my ego from those nasty letters, but once the agent/middleman was out of the equation, those editors were quite friendly with me.

I had two very bad years, years where I’d walk into my office with a “what’s the point?” attitude. Dean got me through them. Dean, and the realization that the other two things I could do—edit and teach—were things I most decidedly did not want to do. (Besides, to teach and make money at it, unlike the workshops that we do which are mostly paying forward, I would have had to go back to college and get a Masters and a PhD, the thought of which gave me the shivers.) I’d edited before, and even though I’m good at it, I hate having someone else dictate what I read.

In those years, I even considered waitressing again. I liked waitressing. Eight hours of scramble, followed by rest. No mind work at all. Very good.I also investigated jobs at the local radio station, which I was overqualified for.

All of the other jobs I could do would pay less and have more aggravation than my writing at its lowest ebb.So I continued writing.

Had I been twenty years younger, I would have jumped. In my twenties, I did jump. Repeatedly. I became a fulltime journalist because I thought it would be easier than fulltime freelancing. (No.)I edited because I thought it was a good base for my freelancing work. (No.)The jobs that worked best—secretarial work and waitressing—were the emergency jobs I got to pay the bills. I still managed to freelance while doing those jobs, and I never ended up hating the work.

It’s been a long hard slog to learn that I’m better suited to be a freelancer than someone’s employee.I’ve learned to weather the setbacks and freelance my way out of them.

My friends who have kept their day jobs have learned the opposite lesson.And fortunately for most of them, they learned that lesson while they still had the excellent day job with the great benefits; they didn’t quit and then realize what they’d lost.

So let’s assume that you’re not running away, that you actually need this job, and you plan to return to freelancing some day.

2. What kind of job should you get? If you don’t need the insurance or the high corporate salary (and honestly, where are you going to get that salary these days with so much talent already looking for that work?), then you should get what I have always called a shit job. Pardon my language here, but it’s apt.

You want a job with no illusions, one that both you and your boss know is a job you’re working because you need the money, not because it’s your career or you hope to advance.

There are a million types of shit jobs out there. My favorite is waitressing. Dean’s favorite is bartending. Other people work retail. Some writers prefer to work in bookstores so that they can keep up with everything that gets published (and have access to free books). Others work as many different kinds of jobs as they can find just to gain the experience for their later writings.I know a lot of people who’ve worked on cruise ships as staff—either in housekeeping or in the casinos or as waiters—just so that they can travel.

Take the best shit job you can find.The best shit jobs are the ones you’ll enjoy while you’re there, but you won’t have any desire (or capability) for advancement.Make sure they’re jobs you can do well (you don’t want to get fired [trust me]), but make sure they’re jobs you won’t regret quitting.

If you get an actual shit job, one that you don’t take home with you (except maybe as a pair of sore feet), then you’ll be able to continue freelancing. When your bank account recovers, when your clients get too numerous to maintain with a full time job, then you will quit—and quit quickly.You don’t want loyalty or the promise of advancement to keep you in what some of my freelancing friends have called “golden shackles.”

3. Benefits. Some of you will have to return to a day job because you need insurance.The cost of health insurance has risen 120% in the past nine years.Some freelance businesses simply cannot afford that kind of increase. Rather than go without insurance, get a job with benefits. Many shit jobs, especially those in resorts or chain businesses, have benefits for employees who work more than 30 hours per week.

If you need health insurance and can no longer afford it on your freelance earnings, bite the bullet and get the day job.Then pray that some form of health care reform passes—even if it’s just one that brings the cost of insurance down for the self-employed.

4. Remember who you are.You’re not a waitress or a bartender. You’re not the guy who fixes copy machines.You’re still that freelance businessperson. In my case, I’m a writer, whether I’m working as (the world’s worst) secretary or not.

Keep your focus on the fact that this day job is to help you through a transition—either to get you on your feet financially or to help you rebuild your business the correct way.

Every single freelancer has to return to a day job at one point or another. That’s part of the career.

And here’s the most important point:

Returning to a day job is not a failure.

In fact, it’s part of your success.You know your limits, manage your money and time well, and know when you need help. Only successful people know how to do that.

That said, it’s hard to return to a day job, particularly if you had a particularly public crash or a very visible business.I’ve watched a lot of retail shops go down in our little resort town this past year, and all of the proprietors have different jobs locally. Some of these people are embarrassed.They won’t meet my gaze, afraid I’ll judge them poorly. Others shrug, blame the economy, and tell me about their e-Bay sales or their plans to reopen when the upturn begins.

Be part of the second category.You may think getting a day job is a setback, but don’t ever call it a failure. Regroup, plan, and start all over again.

See the day job as an opportunity to rebuild your freelance business as something stronger, healthier, and more secure. Maybe build up your savings so that the next time you have a severe setback, you won’t have to return to a day job.Figure out ways to keep expenses down. Analyze what went wrong—and what you did right.

Use the day job as a chance to take a breather from your freelance work. Figure out if you want to go back.

If you do, then realize that this day job is just a stepping stone to a better future.If you believe that the day job is just part of your transition, not a symbol of failure, you’ll move forward and eventually, your freelance business will be a success.

Good stuff, Kris. Even for a person with a day job, it gave me lots to think about. One thing that really changed the dynamic for me, of course, was the kids. Before they came along, I didn’t hesitate to give up a day job and start a bookstore, going a year without any net income and barely making minimum wage the second year. But once the kids came along, my risk tolerance changed.

One thing that really helped me was to stop seeing becoming a full-time writer as a goal in itself and instead a biproduct of reaching a larger goal — like becoming a bestseller, making the Times list, etc. That way I don’t drive myself crazy about it, and the focus is then on the right things — reaching the largest audience possible.

My favorite “fall back” job between freelance gigs has always been to go down and register with the local temp services. Usually minimum wage, and no benefits, true, but very flexible — if you’re not available to work, or don’t want a particular assignment, it’s no issue for them, just means you don’t get paid for that day/week/whatever. When the freelance gigs pick back up, it’s easy to walk away from a temp “career,” because you’re never at an assignment long enough to get attached in any way. You do have to be a bit aggressive to get the first few gigs, but once they get to know you, some services will often call when they have a temp spot that matches your skills. I took so many assignments I was ridiculously overqualified for — printing slogans on lanyards, stuffing fish-food pellets, slapping labels on cosmetics, assembling frozen dinners, not to mention a bazillion office jobs of all sorts. Temping not only paid the bills, it also added to my stock of characters, settings, etc., for future fiction, so had a double benefit!

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